# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_I
_database_code_depnum_ccdc_archive 'CCDC 1841375'
_audit_update_record             
;
2018-05-04 deposited with the CCDC.
2018-10-22 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C24 H17 Cl N2 O3'
_chemical_formula_sum            'C24 H17 Cl N2 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         416.84

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.5002(7)
_cell_length_b                   9.3931(8)
_cell_length_c                   13.1098(11)
_cell_angle_alpha                83.094(2)
_cell_angle_beta                 80.207(2)
_cell_angle_gamma                80.262(2)
_cell_volume                     1012.10(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3563
_cell_measurement_theta_min      1.583
_cell_measurement_theta_max      25.02
_cell_measurement_temperature    297(2)

_exptl_crystal_description       rectangle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             432

_exptl_absorpt_coefficient_mu    0.218
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker,2016/2)'
_exptl_absorpt_correction_T_min  0.69
_exptl_absorpt_correction_T_max  0.75

_diffrn_ambient_temperature      297(2)

_diffrn_source                   'sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            12207
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_theta_min         1.58
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15

_refine_special_details          
;
;

_reflns_number_total             3563
_reflns_number_gt                2899
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0400
_refine_ls_wR_factor_gt          0.1147
_refine_ls_wR_factor_ref         0.1316
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_refine_ls_number_reflns         3563
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0736P)²+0.1488P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.233
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.022(4)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.48031(8) 0.79682(9) 1.23607(4) 0.0947(3) Uani d . . . 1 . .
O O1 0.14995(16) 0.77100(16) 0.84473(13) 0.0733(4) Uani d . . . 1 . .
O O2 0.2205(2) 0.95472(17) 0.91103(13) 0.0813(5) Uani d . . . 1 . .
O O3 0.75379(17) 0.67216(16) 0.57355(10) 0.0712(4) Uani d . . . 1 . .
N N1 0.67966(16) 0.54130(15) 0.83573(10) 0.0467(4) Uani d . . . 1 . .
N N2 0.64209(17) 0.63603(15) 0.74638(10) 0.0475(4) Uani d . . . 1 . .
C C1 -0.0718(3) 0.8853(4) 0.7581(3) 0.1117(10) Uani d . . . 1 . .
H H1A -0.0135 0.9614 0.7244 0.168 Uiso calc U . R 1 . .
H H1B -0.1855 0.9211 0.7678 0.168 Uiso calc U . R 1 . .
H H1C -0.05 0.8056 0.7157 0.168 Uiso calc U . R 1 . .
C C2 -0.0206(3) 0.8363(3) 0.8591(2) 0.1000(9) Uani d . . . 1 . .
H H2A -0.086 0.7655 0.896 0.12 Uiso calc U . R 1 . .
H H2B -0.0359 0.9179 0.9004 0.12 Uiso calc U . R 1 . .
C C3 0.2558(2) 0.8431(2) 0.87060(14) 0.0533(5) Uani d . . . 1 . .
C C4 0.4239(2) 0.76307(18) 0.85025(13) 0.0459(4) Uani d . . . 1 . .
C C5 0.5123(2) 0.72102(19) 0.93932(13) 0.0466(4) Uani d . . . 1 . .
C C6 0.4682(2) 0.7828(2) 1.03329(14) 0.0557(5) Uani d . . . 1 . .
H H6 0.3853 0.8611 1.0401 0.067 Uiso calc U . R 1 . .
C C7 0.5475(2) 0.7278(2) 1.11669(14) 0.0616(5) Uani d . . . 1 . .
C C8 0.6744(2) 0.6160(2) 1.10785(15) 0.0614(5) Uani d . . . 1 . .
H H8 0.7263 0.5801 1.1647 0.074 Uiso calc U . R 1 . .
C C9 0.7244(2) 0.5571(2) 1.01388(14) 0.0545(5) Uani d . . . 1 . .
H H9 0.8128 0.4838 1.0067 0.065 Uiso calc U . R 1 . .
C C10 0.64300(19) 0.60720(18) 0.93037(13) 0.0453(4) Uani d . . . 1 . .
C C11 0.8204(2) 0.44814(18) 0.80076(14) 0.0471(4) Uani d . . . 1 . .
C C12 0.9043(2) 0.3300(2) 0.85372(16) 0.0592(5) Uani d . . . 1 . .
H H12 0.8712 0.3034 0.9237 0.071 Uiso calc U . R 1 . .
C C13 1.0383(2) 0.2539(2) 0.79861(19) 0.0676(6) Uani d . . . 1 . .
H H13 1.0969 0.1753 0.8327 0.081 Uiso calc U . R 1 . .
C C14 1.0884(3) 0.2907(2) 0.69409(18) 0.0716(6) Uani d . . . 1 . .
H H14 1.1798 0.2374 0.6594 0.086 Uiso calc U . R 1 . .
C C15 1.0040(2) 0.4049(2) 0.64165(16) 0.0648(5) Uani d . . . 1 . .
H H15 1.0361 0.429 0.5711 0.078 Uiso calc U . R 1 . .
C C16 0.8691(2) 0.48461(19) 0.69576(14) 0.0509(4) Uani d . . . 1 . .
C C17 0.7571(2) 0.6068(2) 0.65902(13) 0.0511(4) Uani d . . . 1 . .
C C18 0.4900(2) 0.72341(17) 0.75541(13) 0.0459(4) Uani d . . . 1 . .
C C19 0.4139(2) 0.76016(19) 0.66008(13) 0.0485(4) Uani d . . . 1 . .
C C20 0.3830(3) 0.6507(2) 0.60765(16) 0.0651(5) Uani d . . . 1 . .
H H20 0.4161 0.5541 0.6296 0.078 Uiso calc U . R 1 . .
C C21 0.3027(3) 0.6857(3) 0.52256(18) 0.0813(7) Uani d . . . 1 . .
H H21 0.2808 0.6124 0.4878 0.098 Uiso calc U . R 1 . .
C C22 0.2550(3) 0.8288(3) 0.48911(17) 0.0851(7) Uani d . . . 1 . .
H H22 0.2002 0.8516 0.4322 0.102 Uiso calc U . R 1 . .
C C23 0.2879(3) 0.9371(3) 0.53908(17) 0.0792(7) Uani d . . . 1 . .
H H23 0.2575 1.0335 0.5152 0.095 Uiso calc U . R 1 . .
C C24 0.3664(3) 0.9041(2) 0.62533(15) 0.0611(5) Uani d . . . 1 . .
H H24 0.3872 0.9782 0.6598 0.073 Uiso calc U . R 1 . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C7 . 1.7350(19) ?
O1 C3 . 1.322(2) ?
O1 C2 . 1.465(3) ?
O2 C3 . 1.201(2) ?
O3 C17 . 1.213(2) ?
N1 C11 . 1.401(2) ?
N1 C10 . 1.417(2) ?
N1 N2 . 1.4305(19) ?
N2 C17 . 1.395(2) ?
N2 C18 . 1.404(2) ?
C1 C2 . 1.462(4) ?
C1 H1A . 0.96 ?
C1 H1B . 0.96 ?
C1 H1C . 0.96 ?
C2 H2A . 0.97 ?
C2 H2B . 0.97 ?
C3 C4 . 1.494(2) ?
C4 C18 . 1.343(2) ?
C4 C5 . 1.473(2) ?
C5 C6 . 1.392(2) ?
C5 C10 . 1.406(2) ?
C6 C7 . 1.384(3) ?
C6 H6 . 0.93 ?
C7 C8 . 1.372(3) ?
C8 C9 . 1.382(3) ?
C8 H8 . 0.93 ?
C9 C10 . 1.387(2) ?
C9 H9 . 0.93 ?
C11 C16 . 1.387(3) ?
C11 C12 . 1.392(3) ?
C12 C13 . 1.378(3) ?
C12 H12 . 0.93 ?
C13 C14 . 1.384(3) ?
C13 H13 . 0.93 ?
C14 C15 . 1.367(3) ?
C14 H14 . 0.93 ?
C15 C16 . 1.392(3) ?
C15 H15 . 0.93 ?
C16 C17 . 1.453(2) ?
C18 C19 . 1.482(2) ?
C19 C20 . 1.386(3) ?
C19 C24 . 1.388(3) ?
C20 C21 . 1.383(3) ?
C20 H20 . 0.93 ?
C21 C22 . 1.377(4) ?
C21 H21 . 0.93 ?
C22 C23 . 1.364(3) ?
C22 H22 . 0.93 ?
C23 C24 . 1.387(3) ?
C23 H23 . 0.93 ?
C24 H24 . 0.93 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 O1 C2 . . 118.10(19) ?
C11 N1 C10 . . 127.18(14) ?
C11 N1 N2 . . 105.50(13) ?
C10 N1 N2 . . 114.58(13) ?
C17 N2 C18 . . 130.58(14) ?
C17 N2 N1 . . 111.48(13) ?
C18 N2 N1 . . 117.06(13) ?
C2 C1 H1A . . 109.5 ?
C2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C2 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
C1 C2 O1 . . 110.0(2) ?
C1 C2 H2A . . 109.7 ?
O1 C2 H2A . . 109.7 ?
C1 C2 H2B . . 109.7 ?
O1 C2 H2B . . 109.7 ?
H2A C2 H2B . . 108.2 ?
O2 C3 O1 . . 124.27(18) ?
O2 C3 C4 . . 124.09(18) ?
O1 C3 C4 . . 111.51(16) ?
C18 C4 C5 . . 120.62(15) ?
C18 C4 C3 . . 121.54(15) ?
C5 C4 C3 . . 117.74(15) ?
C6 C5 C10 . . 118.42(16) ?
C6 C5 C4 . . 123.53(16) ?
C10 C5 C4 . . 117.97(15) ?
C7 C6 C5 . . 120.07(18) ?
C7 C6 H6 . . 120.0 ?
C5 C6 H6 . . 120.0 ?
C8 C7 C6 . . 121.26(17) ?
C8 C7 Cl1 . . 119.35(15) ?
C6 C7 Cl1 . . 119.34(16) ?
C7 C8 C9 . . 119.54(17) ?
C7 C8 H8 . . 120.2 ?
C9 C8 H8 . . 120.2 ?
C8 C9 C10 . . 120.11(18) ?
C8 C9 H9 . . 119.9 ?
C10 C9 H9 . . 119.9 ?
C9 C10 C5 . . 120.50(16) ?
C9 C10 N1 . . 122.24(15) ?
C5 C10 N1 . . 117.13(14) ?
C16 C11 C12 . . 120.59(17) ?
C16 C11 N1 . . 109.49(14) ?
C12 C11 N1 . . 129.85(17) ?
C13 C12 C11 . . 117.57(19) ?
C13 C12 H12 . . 121.2 ?
C11 C12 H12 . . 121.2 ?
C12 C13 C14 . . 122.05(19) ?
C12 C13 H13 . . 119.0 ?
C14 C13 H13 . . 119.0 ?
C15 C14 C13 . . 120.33(19) ?
C15 C14 H14 . . 119.8 ?
C13 C14 H14 . . 119.8 ?
C14 C15 C16 . . 118.8(2) ?
C14 C15 H15 . . 120.6 ?
C16 C15 H15 . . 120.6 ?
C11 C16 C15 . . 120.68(17) ?
C11 C16 C17 . . 109.31(15) ?
C15 C16 C17 . . 129.98(18) ?
O3 C17 N2 . . 124.62(16) ?
O3 C17 C16 . . 131.16(16) ?
N2 C17 C16 . . 104.20(15) ?
C4 C18 N2 . . 117.25(15) ?
C4 C18 C19 . . 125.56(15) ?
N2 C18 C19 . . 117.17(14) ?
C20 C19 C24 . . 119.53(17) ?
C20 C19 C18 . . 120.06(16) ?
C24 C19 C18 . . 120.34(16) ?
C21 C20 C19 . . 119.79(19) ?
C21 C20 H20 . . 120.1 ?
C19 C20 H20 . . 120.1 ?
C22 C21 C20 . . 120.3(2) ?
C22 C21 H21 . . 119.9 ?
C20 C21 H21 . . 119.9 ?
C23 C22 C21 . . 120.3(2) ?
C23 C22 H22 . . 119.9 ?
C21 C22 H22 . . 119.9 ?
C22 C23 C24 . . 120.3(2) ?
C22 C23 H23 . . 119.9 ?
C24 C23 H23 . . 119.9 ?
C23 C24 C19 . . 119.86(19) ?
C23 C24 H24 . . 120.1 ?
C19 C24 H24 . . 120.1 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C11 N1 N2 C17 . . . . -1.69(18) ?
C10 N1 N2 C17 . . . . 143.04(15) ?
C11 N1 N2 C18 . . . . 168.71(14) ?
C10 N1 N2 C18 . . . . -46.56(19) ?
C3 O1 C2 C1 . . . . 108.7(3) ?
C2 O1 C3 O2 . . . . 4.7(3) ?
C2 O1 C3 C4 . . . . -179.37(18) ?
O2 C3 C4 C18 . . . . -127.5(2) ?
O1 C3 C4 C18 . . . . 56.6(2) ?
O2 C3 C4 C5 . . . . 56.1(2) ?
O1 C3 C4 C5 . . . . -119.87(17) ?
C18 C4 C5 C6 . . . . 165.70(17) ?
C3 C4 C5 C6 . . . . -17.8(2) ?
C18 C4 C5 C10 . . . . -17.7(2) ?
C3 C4 C5 C10 . . . . 158.79(15) ?
C10 C5 C6 C7 . . . . -2.9(3) ?
C4 C5 C6 C7 . . . . 173.66(16) ?
C5 C6 C7 C8 . . . . 2.5(3) ?
C5 C6 C7 Cl1 . . . . -174.90(14) ?
C6 C7 C8 C9 . . . . 0.2(3) ?
Cl1 C7 C8 C9 . . . . 177.61(15) ?
C7 C8 C9 C10 . . . . -2.4(3) ?
C8 C9 C10 C5 . . . . 2.0(3) ?
C8 C9 C10 N1 . . . . -173.85(16) ?
C6 C5 C10 C9 . . . . 0.7(2) ?
C4 C5 C10 C9 . . . . -176.07(15) ?
C6 C5 C10 N1 . . . . 176.73(15) ?
C4 C5 C10 N1 . . . . -0.1(2) ?
C11 N1 C10 C9 . . . . -17.9(3) ?
N2 N1 C10 C9 . . . . -153.58(15) ?
C11 N1 C10 C5 . . . . 166.20(15) ?
N2 N1 C10 C5 . . . . 30.5(2) ?
C10 N1 C11 C16 . . . . -137.84(17) ?
N2 N1 C11 C16 . . . . 0.94(18) ?
C10 N1 C11 C12 . . . . 45.3(3) ?
N2 N1 C11 C12 . . . . -175.96(17) ?
C16 C11 C12 C13 . . . . 1.4(3) ?
N1 C11 C12 C13 . . . . 178.02(17) ?
C11 C12 C13 C14 . . . . -0.8(3) ?
C12 C13 C14 C15 . . . . -0.5(3) ?
C13 C14 C15 C16 . . . . 1.1(3) ?
C12 C11 C16 C15 . . . . -0.8(3) ?
N1 C11 C16 C15 . . . . -178.03(17) ?
C12 C11 C16 C17 . . . . 177.32(16) ?
N1 C11 C16 C17 . . . . 0.08(19) ?
C14 C15 C16 C11 . . . . -0.5(3) ?
C14 C15 C16 C17 . . . . -178.19(19) ?
C18 N2 C17 O3 . . . . 11.7(3) ?
N1 N2 C17 O3 . . . . -179.60(18) ?
C18 N2 C17 C16 . . . . -167.01(17) ?
N1 N2 C17 C16 . . . . 1.71(18) ?
C11 C16 C17 O3 . . . . -179.7(2) ?
C15 C16 C17 O3 . . . . -1.8(4) ?
C11 C16 C17 N2 . . . . -1.09(19) ?
C15 C16 C17 N2 . . . . 176.80(19) ?
C5 C4 C18 N2 . . . . 2.6(2) ?
C3 C4 C18 N2 . . . . -173.71(15) ?
C5 C4 C18 C19 . . . . -179.40(15) ?
C3 C4 C18 C19 . . . . 4.3(3) ?
C17 N2 C18 C4 . . . . -162.42(18) ?
N1 N2 C18 C4 . . . . 29.4(2) ?
C17 N2 C18 C19 . . . . 19.4(3) ?
N1 N2 C18 C19 . . . . -148.76(15) ?
C4 C18 C19 C20 . . . . -119.3(2) ?
N2 C18 C19 C20 . . . . 58.7(2) ?
C4 C18 C19 C24 . . . . 57.8(3) ?
N2 C18 C19 C24 . . . . -124.24(18) ?
C24 C19 C20 C21 . . . . -1.2(3) ?
C18 C19 C20 C21 . . . . 175.91(19) ?
C19 C20 C21 C22 . . . . 0.7(4) ?
C20 C21 C22 C23 . . . . 0.6(4) ?
C21 C22 C23 C24 . . . . -1.4(4) ?
C22 C23 C24 C19 . . . . 0.9(3) ?
C20 C19 C24 C23 . . . . 0.4(3) ?
C18 C19 C24 C23 . . . . -176.72(18) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C6 H6 O2 . 0.93 2.37 2.997(3) 124.4 ?

